Buprenorphine

Identification

Summary

Buprenorphine is a partial opioid agonist used for management of severe pain that is not responsive to alternative treatments. Also used for maintenance treatment of opioid addiction.

Brand Names

Belbuca, Brixadi, Buprenex, Buprenorphine, Butrans, Sublocade, Suboxone, Subutex, Zubsolv

Generic Name

Buprenorphine

DrugBank Accession Number

DB00921

Background

Buprenorphine is a weak partial mu-opioid receptor agonist and a weak kappa-opioid receptor antagonist used for the treatment of severe pain.^12,15 It is also commonly used as an alternative to methadone for the treatment of severe opioid addiction.²² Buprenorphine is commercially available as the brand name product Suboxone which is formulated in a 4:1 fixed-dose combination product along with naloxone, a non-selective competitive opioid receptor antagonist. Combination with naloxone is intended to reduce the abuse potential of Suboxone, as naloxone is poorly absorbed by the oral route (and has no effect when taken orally), but would reverse the opioid agonist effects of buprenorphine if injected intravenously.^14,22 Buprenorphine has poor gastrointestinal absorption and is therefore formulated as a sublingual tablet.

Buprenorphine has a number of unique pharmacokinetic and pharmacodynamic properties that make it a preferred agent for the treatment of conditions requiring high doses of strong opioids.¹³ For example, buprenorphine dissociates from opioid receptors very slowly, resulting in a long duration of action and relief from pain or withdrawal symptoms for upwards of 24-36 hours. Use of once-daily buprenorphine may benefit individuals who have developed tolerance to other potent opioids and who require larger and more frequent doses. Buprenorphine may also be a preferred agent over methadone (which is also commonly used to treat severe pain and opioid use disorder), as it has less effect on Qtc interval prolongation,^9,10 fewer drug interactions, reduced risk of sexual side effects,¹⁷ and an improved safety profile with a lower risk of overdose and respiratory depression.^6,7,8

Buprenorphine acts as a partial mu-opioid receptor agonist with a high affinity for the receptor, but lower intrinsic activity compared to other full mu-opioid agonists such as heroin, oxycodone, or methadone.¹⁵ This means that buprenorphine preferentially binds the opioid receptor and displaces lower affinity opioids without activating the receptor to a comparable degree. Clinically, this results in a slow onset of action and a clinical phenomenon known as the "ceiling effect" where once a certain dose is reached, buprenorphine's effects plateau. This effect can be beneficial, however, as dose-related side effects such as respiratory depression, sedation, and intoxication also plateau at around 32mg, resulting in a lower risk of overdose compared to methadone and other full agonist opioids.^4,5 It also means that opioid-dependent patients do not experience sedation or euphoria at the same rate that they might experience with more potent opioids, improving quality of life for patients with severe pain and reducing the reinforcing effects of opioids which can lead to drug-seeking behaviours.¹¹

Treatment of opioid addiction with buprenorphine, methadone, or slow-release oral morphine (SROM) is termed Opioid Agonist Treatment (OAT) or Opioid Substitution Therapy (OST). The intention of substitution of illicit opioids with the long-acting opioids used in OAT is to prevent withdrawal symptomns for 24-36 hours following dosing to ultimately reduce cravings and drug-seeking behaviours. Use of OAT is also intended to improved social stabilization including a reduction in crime rates, marginalization, incarceration, and use of illicit substances such as heroin or fentanyl. Illegally purchased opioids can often be injected and may be laced with other substances that increase the risk of harm or overdose. Provision of OAT is often combined with education about harm reduction including use of clean needles and injection supplies in an effort to reduce the risks associated with injection drug use which includes contraction of HIV and Hepatitis C and other complications including skin infections, abscesses, or endocarditis.¹⁶

Type

Small Molecule

Groups

Approved, Illicit, Investigational, Vet approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Buprenorphine (DB00921)

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Weight

Average: 467.6401
Monoisotopic: 467.303558805

Chemical Formula

C₂₉H₄₁NO₄

Synonyms

• (−)-buprenorphine
• 17-cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol
• 2-(N-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol
• 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanol
• 21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
• Buprenophine
• Buprenorfina
• Buprenorphine
• Buprenorphinum

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Pharmacology

Indication

Buprenorphine is available in different formulations, such as sublingual tablets, buccal films, transdermal films, and injections, alone or in combination with naloxone.

The buccal film, intramuscular or intravenous injection, and transdermal formulation are indicated for the management of pain severe enough to require an opioid analgesic and for which alternate treatments are inadequate.^21,23,24

The extended-release subcutaneous injections of buprenorphine are indicated for the treatment of moderate to severe opioid use disorder in patients who have initiated treatment with a single dose of a transmucosal buprenorphine product or who are already being treated with buprenorphine. Injections are part of a complete treatment plan that includes counselling and psychosocial support.²⁰

Sublingual tablets and buccal films, in combination with naloxone, are indicated for the maintenance treatment of opioid dependence as part of a complete treatment plan that includes counselling and psychosocial support.^19,22

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used as adjunct in combination to treat	Opioid dependence	Combination Product in combination with: Naloxone (DB01183)	••••••••••••
Management of	Severe pain		••••••••••••			•••••••••
Adjunct therapy in treatment of	Moderate opioid dependence		••••••••••••			•••••••••• ••••••••••• •••••••• •••••••
Management of	Moderate pain		••••••••••••			•••••••••
Adjunct therapy in treatment of	Severe opioid dependence		••••••••••••			•••••••••• ••••••••••• •••••••• •••••••

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Pharmacodynamics

Buprenorphine interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, buprenorphine exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Buprenorphine depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.

Dependence

Buprenorphine is a partial agonist at the mu-opioid receptor and chronic administration produces physical dependence of the opioid type, characterized by withdrawal signs and symptoms upon abrupt discontinuation or rapid taper. The withdrawal syndrome is typically milder than seen with full agonists and may be delayed in onset. Buprenorphine can be abused in a manner similar to other opioids. This should be considered when prescribing or dispensing buprenorphine in situations when the clinician is concerned about an increased risk of misuse, abuse, or diversion.[F4718]

Withdrawal

Abrupt discontinuation of treatment is not recommended as it may result in an opioid withdrawal syndrome that may be delayed in onset. Signs and symptoms may include body aches, diarrhea, gooseflesh, loss of appetite, nausea, nervousness or restlessness, anxiety, runny nose, sneezing, tremors or shivering, stomach cramps, tachycardia, trouble with sleeping, unusual increase in sweating, palpitations, unexplained fever, weakness and yawning.[F4718]

Risk of Respiratory and Central Nervous System (CNS) Depression and Overdose

Buprenorphine has been associated with life-threatening respiratory depression and death. Many, but not all, post-marketing reports regarding coma and death involved misuse by self-injection or were associated with the concomitant use of buprenorphine and benzodiazepines or other CNS depressant, including alcohol. Use buprenorphine and naloxone sublingual tablets with caution in patients with compromised respiratory function (e.g., chronic obstructive pulmonary disease, cor pulmonale, decreased respiratory reserve, hypoxia, hypercapnia, or pre-existing respiratory depression).²²

Risk of Overdose in Opioid Naïve Patients

There have been reported deaths of opioid-naïve individuals who received a 2 mg dose of buprenorphine as a sublingual tablet for analgesia. Buprenorphine and naloxone sublingual tablets are not appropriate as an analgesic in opioid-naïve patients.²²

Precipitation of Opioid Withdrawal Signs and Symptoms

If buprenorphine is started in opioid-dependent individuals, it will displace the other opioids and cause a phenomenon known as "precipitated withdrawal" which is characterized by a rapid and intense onset of withdrawal symptoms. Individuals must therefore be in a state of mild to moderate withdrawal before starting therapy with buprenorphine.

Because it contains naloxone, buprenorphine and naloxone sublingual tablets are also highly likely to produce marked and intense withdrawal signs and symptoms if misused parenterally by individuals dependent on full opioid agonists such as heroin, morphine, or methadone.²²

Gastrointestinal Effects

Buprenorphine and other morphine-like opioids have been shown to decrease bowel motility and cause constipation. Buprenorphine may obscure the diagnosis or clinical course of patients with acute abdominal conditions and should be administered with caution to patients with dysfunction of the biliary tract.²²

Effects on the Endocrine System

Opioids inhibit the secretion of adrenocorticotropic hormone (ACTH), cortisol, and luteinizing hormone (LH) in humans. They also stimulate prolactin, growth hormone (GH) secretion, and pancreatic secretion of insulin and glucagon. Chronic use of opioids may influence the hypothalamic-pituitary-gonadal axis, leading to androgen deficiency that may manifest as low libido, impotence, erectile dysfunction, amenorrhea, or infertility. The causal role of opioids in the clinical syndrome of hypogonadism is unknown because the various medical, physical, lifestyle, and psychological stressors that may influence gonadal hormone levels have not been adequately controlled for in studies conducted to date. Patients presenting with symptoms of androgen deficiency should undergo laboratory evaluation.²²

Adrenal Insufficiency

Cases of adrenal insufficiency have been reported with opioid use, more often following greater than one month of use. Presentation of adrenal insufficiency may include non-specific symptoms and signs including nausea, vomiting, anorexia, fatigue, weakness, dizziness, and low blood pressure. If adrenal insufficiency is suspected, confirm the diagnosis with diagnostic testing as soon as possible. If adrenal insufficiency is diagnosed, treat with physiologic replacement doses of corticosteroids. Wean the patient off of the opioid to allow adrenal function to recover and continue corticosteroid treatment until adrenal function recovers. Other opioids may be tried as some cases reported use of a different opioid without recurrence of adrenal insufficiency. The information available does not identify any particular opioids as being more likely to be associated with adrenal insufficiency.²²

Use in Patients With Impaired Hepatic Function

Buprenorphine/naloxone products are not recommended in patients with severe hepatic impairment and may not be appropriate for patients with moderate hepatic impairment. The doses of buprenorphine and naloxone in this fixed-dose combination product cannot be individually titrated, and hepatic impairment results in a reduced clearance of naloxone to a much greater extent than buprenorphine. Therefore, patients with severe hepatic impairment will be exposed to substantially higher levels of naloxone than patients with normal hepatic function. This may result in an increased risk of precipitated withdrawal at the beginning of treatment (induction) and may interfere with buprenorphine’s efficacy throughout treatment. In patients with moderate hepatic impairment, the differential reduction of naloxone clearance compared to buprenorphine clearance is not as great as in subjects with severe hepatic impairment. However, buprenorphine/naloxone products are not recommended for initiation of (treatment induction) in patients with moderate hepatic impairment due to the increased risk of precipitated withdrawal. Buprenorphine/naloxone products may be used with caution for maintenance treatment in patients with moderate hepatic impairment who have initiated treatment on a buprenorphine product without naloxone. However, patients should be carefully monitored and consideration given to the possibility of naloxone interfering with buprenorphine’s efficacy.²²

Risk of Hepatitis, Hepatic Events

Cases of cytolytic hepatitis and hepatitis with jaundice have been observed in individuals receiving buprenorphine in clinical trials and through post-marketing adverse event reports. The spectrum of abnormalities ranges from transient asymptomatic elevations in hepatic transaminases to case reports of death, hepatic failure, hepatic necrosis, hepatorenal syndrome, and hepatic encephalopathy. In many cases, the presence of pre-existing liver enzyme abnormalities, infection with hepatitis B or hepatitis C virus, concomitant usage of other potentially hepatotoxic drugs, and ongoing injecting drug use may have played a causative or contributory role. In other cases, insufficient data were available to determine the etiology of the abnormality. Withdrawal of buprenorphine has resulted in amelioration of acute hepatitis in some cases; however, in other cases no dose reduction was necessary. The possibility exists that buprenorphine had a causative or contributory role in the development of the hepatic abnormality in some cases. Liver function tests, prior to initiation of treatment is recommended to establish a baseline. Periodic monitoring of liver function during treatment is also recommended. A biological and etiological evaluation is recommended when a hepatic event is suspected. Depending on the case, buprenorphine and naloxone sublingual tablets may need to be carefully discontinued to prevent withdrawal signs and symptoms and a return by the patient to illicit drug use, and strict monitoring of the patient should be initiated.²²

Orthostatic Hypotension

Like other opioids, buprenorphine and naloxone sublingual tablets may produce orthostatic hypotension in ambulatory patients.

Elevation of Cerebrospinal Fluid Pressure

Buprenorphine, like other opioids, may elevate cerebrospinal fluid pressure and should be used with caution in patients with head injury, intracranial lesions, and other circumstances when cerebrospinal pressure may be increased. Buprenorphine can produce miosis and changes in the level of consciousness that may interfere with patient evaluation.

Elevation of Intracholedochal Pressure

Buprenorphine has been shown to increase intracholedochal pressure, as do other opioids, and thus should be administered with caution to patients with dysfunction of the biliary tract.

Mechanism of action

Buprenorphine is a partial agonist at the mu-opioid receptor and an antagonist at the kappa-opioid receptor. It demonstrates a high affinity for the mu-opioid receptor but has lower intrinsic activity compared to other full mu-opioid agonists such as heroin, oxycodone, or methadone.¹⁵ This means that buprenorphine preferentially binds the opioid receptor and displaces lower affinity opioids without activating the receptor to a comparable degree. Clinically, this results in a slow onset of action and a clinical phenomenon known as the "ceiling effect" where once a certain dose is reached buprenorphine's effects plateau. This effect can be beneficial, however, as dose-related side effects such as respiratory depression, sedation, and intoxication also plateau at around 32mg, resulting in a lower risk of overdose compared to methadone and other full agonist opioids.^4,5 It also means that opioid-dependent patients do not experience sedation or euphoria at the same rate that they might experience with more potent opioids, improving quality of life for patients with severe pain and reducing the reinforcing effects of opioids which can lead to drug-seeking behaviours.¹¹

Buprenorphine's high affinity, but low intrinsic activity for the mu-opioid receptor also means that if it is started in opioid-dependent individuals, it will displace the other opioids without creating an equal opioid effect and cause a phenomenon known as "precipitated withdrawal" which is characterized by a rapid and intense onset of withdrawal symptoms (i.e. anxiety, restlessness, gastrointestinal distress, diaphoresis, intense drug cravings, and tachycardia). Individuals must therefore be in a state of mild to moderate withdrawal before starting therapy with buprenorphine.

Buprenorphine is commercially available as the brand name product Suboxone which is formulated in a 4:1 fixed-dose combination product along with naloxone, a non-selective competitive opioid receptor antagonist. Combination of an opioid agonist with an opioid antagonist may seem counterintuitive, however this combination with naloxone is intended to reduce the abuse potential of Suboxone, as naloxone is poorly absorbed by the oral route (and has no effect when taken orally), but would reverse the opioid agonist effects of buprenorphine if injected intravenously.^14,22

Target	Actions	Organism
AKappa-type opioid receptor	antagonist	Humans
AMu-type opioid receptor	partial agonist	Humans
UDelta-type opioid receptor	antagonist	Humans
UNociceptin receptor	Not Available	Humans

Absorption

Bioavailablity of buprenorphine/naloxone is very high following intravenous or subcutaneous administration, lower by the sublingual or buccal route, and very low when administered by the oral route. It is therefore provided as a sublingual tablet that is absorbed from the oral mucosa directly into systemic circulation.¹⁸

Clinical pharmacokinetic studies found that there was wide inter-patient variability in the sublingual absorption of buprenorphine and naloxone, but within subjects the variability was low. Both Cmax and AUC of buprenorphine increased in a linear fashion with the increase in dose (in the range of 4 to 16 mg), although the increase was not directly dose-proportional. Buprenorphine combination with naloxone (2mg/0.5mg) provided in sublingual tablets demonstrated a Cmax of 0.780 ng/mL with a Tmax of 1.50 hr and AUC of 7.651 ng.hr/mL.²²

Coadministration with naloxone does not effect the pharmacokinetics of buprenorphine.

Volume of distribution

Buprenorphine is highly lipophilic, and therefore extensively distributed, with rapid penetration through the blood-brain barrier. The estimated volume of distribution is 188 - 335 L when given intravenously. It is able to cross into the placenta and breast milk.

Protein binding

Buprenorphine is approximately 96% protein-bound, primarily to alpha- and beta-globulin.²²

Metabolism

Buprenorphine is metabolized to norbuprenorphine via Cytochrome P450 3A4/3A5-mediated N-dealkylation. Buprenorphine and norbuprenorphine both also undergo glucuronidation to the inactive metabolites buprenorphine-3-glucuronide and norbuprenorphine-3-glucuronide, respectively.^18,22

While norbuprenorphine has been found to bind to opioid receptors in-vitro, brain concentrations are very low which suggests that it does not contribute to the clinical effects of buprenorphine.¹⁸

Naloxone undergoes direct glucuronidation to naloxone-3-glucuronide as well as N-dealkylation, and reduction of the 6-oxo group.²²

Hover over products below to view reaction partners

• Buprenorphine
  • Norbuprenorphine
    • Hydroxynorbuprenorphine
  • Hydroxybuprenorphine
    • Hydroxynorbuprenorphine
  • Buprenorphine glucuronide

Route of elimination

Buprenorphine, like morphine and other phenolic opioid analgesics, is metabolized by the liver and its clearance is related to hepatic blood flow. It is primarily eliminated via feces (as free forms of buprenorphine and norbuprenorphine) while 10 - 30% of the dose is excreted in urine (as conjugated forms of buprenorphine and norbuprenorphine).²²

The overall mean elimination half-life of buprenorphine in plasma ranges from 31 to 42 hours, although the levels are very low 10 hours after dosing (majority of AUC of buprenorphine is captured within 10 hours), indicating that the effective half-life may be shorter.²²

Half-life

Buprenorphine demonstrates slow dissociation kinetics (~166 min), which contributes to its long duration of action and allows for once-daily or even every-second-day dosing.¹⁸ In clinical trial studies, the half-life of sublingually administered buprenorphine/naloxone 2mg/0.5mg was found to be 30.75 hours.²²

Clearance

Clearance may be higher in children than in adults. Plasma clearance rate, IV administration, anaesthetized patients = 901.2 ± 39.7 mL/min; Plasma clearance rate, IV administration, healthy subjects = 1042 - 1280 mL/min.

Adverse Effects

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Toxicity

Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.

Pathways

Pathway	Category
Buprenorphine Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
Abametapir	The serum concentration of Buprenorphine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Buprenorphine can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Buprenorphine.
Abiraterone	The metabolism of Buprenorphine can be decreased when combined with Abiraterone.

Food Interactions

• Avoid alcohol. Ingesting alcohol may increase the sedative and CNS depressant effects of buprenorphine.
• Avoid grapefruit products. Grapefruit inhibits the metabolism of buprenorphine through CYP3A4, which increases the serum levels buprenorphine.
• Take separate from meals. When buprenorphine is formulated as a sublingual tablet or buccal film, avoid eating or drinking until the dosage form is completely dissolved.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Buprenorphine hydrochloride	56W8MW3EN1	53152-21-9	UAIXRPCCYXNJMQ-RZIPZOSSSA-N

Product Images

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International/Other Brands

Addnok (Rusan Pharma Ltd.) / Buprel / Buprigesic (Neon Laboratories) / Morgesic (Samarth Pharma) / Norphin (Unichem Laboratories) / Norspan / Temgesic / Tidigesic (Sun Pharmaceuticals)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Belbuca	Film, soluble	300 ug/1	Buccal	BioDelivery Sciences International Inc	2017-09-01	Not applicable
Belbuca	Film	600 ug/1	Buccal	Endo Pharmaceuticals	2015-06-01	2019-06-30
Belbuca	Film	150 ug/1	Buccal	Endo Pharmaceuticals	2015-06-01	2019-06-30
Belbuca	Film, soluble	450 ug/1	Buccal	Quality Care Products, LLC	2020-06-02	Not applicable
Belbuca	Film	900 ug/1	Buccal	Endo Pharmaceuticals	2015-06-01	2019-06-30

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Bar-buprenorphine	Patch	10 mcg / hour	Transdermal	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-buprenorphine	Patch	20 mcg / hour	Transdermal	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-buprenorphine	Patch	5 mcg / hour	Transdermal	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Bar-buprenorphine	Patch	15 mcg / hour	Transdermal	Bard Pharmaceuticals (1990) Inc	Not applicable	Not applicable
Buprenorphene	Patch, extended release	20 ug/1h	Transdermal	Apotex Corp.	2021-10-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Bunavail	Buprenorphine hydrochloride (4.2 mg/1) + Naloxone hydrochloride dihydrate (0.7 mg/1)	Film	Buccal	BioDelivery Sciences International, Inc.	2014-09-30	2021-10-31
Bunavail	Buprenorphine hydrochloride (2.1 mg/1) + Naloxone hydrochloride dihydrate (0.3 mg/1)	Film	Buccal	BioDelivery Sciences International, Inc.	2014-09-30	2021-02-28
Bunavail	Buprenorphine hydrochloride (6.3 mg/1) + Naloxone hydrochloride dihydrate (1 mg/1)	Film	Buccal	BioDelivery Sciences International, Inc.	2014-09-30	2021-07-31
Bupensan Duo 2 mg/0,5 mg-Sublingualtabletten	Buprenorphine hydrochloride (2 mg) + Naloxone hydrochloride dihydrate (0.5 mg)	Tablet, orally disintegrating	Sublingual	G.L. Pharma Gmb H	2018-06-06	Not applicable
Bupensan Duo 4 mg/1 mg-Sublingualtabletten	Buprenorphine hydrochloride (4 mg) + Naloxone hydrochloride dihydrate (1 mg)	Tablet, orally disintegrating	Sublingual	G.L. Pharma Gmb H	2018-06-06	Not applicable

Categories

ATC Codes

N07BC01 — Buprenorphine

• N07BC — Drugs used in opioid dependence
• N07B — DRUGS USED IN ADDICTIVE DISORDERS
• N07 — OTHER NERVOUS SYSTEM DRUGS
• N — NERVOUS SYSTEM

N07BC51 — Buprenorphine, combinations

• N07BC — Drugs used in opioid dependence
• N07B — DRUGS USED IN ADDICTIVE DISORDERS
• N07 — OTHER NERVOUS SYSTEM DRUGS
• N — NERVOUS SYSTEM

N02AE01 — Buprenorphine

• N02AE — Oripavine derivatives
• N02A — OPIOIDS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

Drug Categories

• Alkaloids
• Analgesics
• BCRP/ABCG2 Inhibitors
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP2C18 Substrates
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (weak)
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (weak)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A7 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs Used in Addictive Disorders
• Drugs Used in Opioid Dependence
• Heterocyclic Compounds, Fused-Ring
• Mixed Agonist / Antagonist Opioids
• Morphinans
• Narcotics
• Nervous System
• Opiate Agonists
• Opiate Alkaloids
• Opiate Partial Agonists
• Opioid Antagonists
• Opioids
• Oripavine Derivatives
• P-glycoprotein inhibitors
• Peripheral Nervous System Agents
• Phenanthrenes
• Sensory System Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
• UGT1A1 Substrates
• UGT1A9 Substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Tetralins / Azaspirodecane derivatives / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Tertiary alcohols / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives

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Substituents

1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azaspirodecane / Coumaran / Dialkyl ether / Ether / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Phenanthrene / Piperidine / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine / Tetralin

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:3216)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

40D3SCR4GZ

CAS number

52485-79-7

InChI Key

RMRJXGBAOAMLHD-IHFGGWKQSA-N

InChI

InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1

IUPAC Name

(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol

SMILES

CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1CC1CC1)=C(O)C=C4

References

Synthesis Reference

Kazuhisa Ninomiya, Yasuhiro Fukushima, Mutsuo Okumura, Yuko Hosokawa, "Buprenorphine percutaneous absorption preparation." U.S. Patent US6090405, issued August, 1992.

US6090405

General References

1. Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. [Article]
2. Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. [Article]
3. Elkader A, Sproule B: Buprenorphine: clinical pharmacokinetics in the treatment of opioid dependence. Clin Pharmacokinet. 2005;44(7):661-80. [Article]
4. Dahan A, Yassen A, Bijl H, Romberg R, Sarton E, Teppema L, Olofsen E, Danhof M: Comparison of the respiratory effects of intravenous buprenorphine and fentanyl in humans and rats. Br J Anaesth. 2005 Jun;94(6):825-34. doi: 10.1093/bja/aei145. Epub 2005 Apr 15. [Article]
5. Walsh SL, Preston KL, Stitzer ML, Cone EJ, Bigelow GE: Clinical pharmacology of buprenorphine: ceiling effects at high doses. Clin Pharmacol Ther. 1994 May;55(5):569-80. doi: 10.1038/clpt.1994.71. [Article]
6. Bruneau J, Ahamad K, Goyer ME, Poulin G, Selby P, Fischer B, Wild TC, Wood E: Management of opioid use disorders: a national clinical practice guideline. CMAJ. 2018 Mar 5;190(9):E247-E257. doi: 10.1503/cmaj.170958. [Article]
7. Luty J, O'Gara C, Sessay M: Is methadone too dangerous for opiate addiction? BMJ. 2005 Dec 10;331(7529):1352-3. doi: 10.1136/bmj.331.7529.1352. [Article]
8. Marteau D, McDonald R, Patel K: The relative risk of fatal poisoning by methadone or buprenorphine within the wider population of England and Wales. BMJ Open. 2015 May 29;5(5):e007629. doi: 10.1136/bmjopen-2015-007629. [Article]
9. Wedam EF, Bigelow GE, Johnson RE, Nuzzo PA, Haigney MC: QT-interval effects of methadone, levomethadyl, and buprenorphine in a randomized trial. Arch Intern Med. 2007 Dec 10;167(22):2469-75. doi: 10.1001/archinte.167.22.2469. [Article]
10. Anchersen K, Clausen T, Gossop M, Hansteen V, Waal H: Prevalence and clinical relevance of corrected QT interval prolongation during methadone and buprenorphine treatment: a mortality assessment study. Addiction. 2009 Jun;104(6):993-9. doi: 10.1111/j.1360-0443.2009.02549.x. Epub 2009 Apr 9. [Article]
11. Tzschentke TM: Behavioral pharmacology of buprenorphine, with a focus on preclinical models of reward and addiction. Psychopharmacology (Berl). 2002 Apr;161(1):1-16. doi: 10.1007/s00213-002-1003-8. Epub 2002 Mar 6. [Article]
12. Lutfy K, Eitan S, Bryant CD, Yang YC, Saliminejad N, Walwyn W, Kieffer BL, Takeshima H, Carroll FI, Maidment NT, Evans CJ: Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors. J Neurosci. 2003 Nov 12;23(32):10331-7. [Article]
13. Johnson RE, Strain EC, Amass L: Buprenorphine: how to use it right. Drug Alcohol Depend. 2003 May 21;70(2 Suppl):S59-77. doi: 10.1016/s0376-8716(03)00060-7. [Article]
14. Orman JS, Keating GM: Buprenorphine/naloxone: a review of its use in the treatment of opioid dependence. Drugs. 2009;69(5):577-607. doi: 10.2165/00003495-200969050-00006. [Article]
15. Lutfy K, Cowan A: Buprenorphine: a unique drug with complex pharmacology. Curr Neuropharmacol. 2004 Oct;2(4):395-402. doi: 10.2174/1570159043359477. [Article]
16. Toce MS, Chai PR, Burns MM, Boyer EW: Pharmacologic Treatment of Opioid Use Disorder: a Review of Pharmacotherapy, Adjuncts, and Toxicity. J Med Toxicol. 2018 Dec;14(4):306-322. doi: 10.1007/s13181-018-0685-1. Epub 2018 Oct 30. [Article]
17. Yee A, Loh HS, Hisham Hashim HM, Ng CG: Clinical factors associated with sexual dysfunction among men in methadone maintenance treatment and buprenorphine maintenance treatment: a meta-analysis study. Int J Impot Res. 2014 Sep-Oct;26(5):161-6. doi: 10.1038/ijir.2014.18. Epub 2014 Jul 3. [Article]
18. Coe MA, Lofwall MR, Walsh SL: Buprenorphine Pharmacology Review: Update on Transmucosal and Long-acting Formulations. J Addict Med. 2019 Mar/Apr;13(2):93-103. doi: 10.1097/ADM.0000000000000457. [Article]
19. FDA Approved Drug Products: Bunavail (buprenorphine and naloxone) Sublingual, Buccal Film [Link]
20. FDA Approved Drug Products: BRIXADI (buprenorphine) extended-release injection for subcutaneous use CIII (May 2023) [Link]
21. FDA Approved Drug Products: BUPRENEX (buprenorphine hydrochloride) injection, for intravenous or intramuscular administration, CIII (June 2022) [Link]
22. FDA Approved Drug Products: SUBOXONE (buprenorphine and naloxone) sublingual tablets, CIII (June 2022) [Link]
23. FDA Approved Drug Products: BELBUCA (buprenorphine buccal film), CIII (June 2022) [Link]
24. FDA Approved Drug Products: BUTRANS (buprenorphine) transdermal system, CIII (June 2022) [Link]
25. FDA Approved Drug Products: SUBLOCADE (buprenorphine extended‐release) injection, for subcutaneous use, CIII (December 2023) [Link]

External Links

Human Metabolome Database

HMDB0015057

KEGG Drug

D07132

KEGG Compound

C08007

PubChem Compound

644073

PubChem Substance

46505782

ChemSpider

559124

BindingDB

50026603

RxNav

1819

ChEBI

3216

ChEMBL

CHEMBL560511

ZINC

ZINC000001319780

Therapeutic Targets Database

DAP001353

PharmGKB

PA448685

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Buprenorphine

FDA label

Download (345 KB)

MSDS

Download (196 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Moderate to Severe Opioid-use Disorder	1
4	Completed	Basic Science	Healthy Subjects (HS)	1
4	Completed	Health Services Research	Human Immunodeficiency Virus (HIV) Infections / Opioid Use Disorder (OUD)	1
4	Completed	Supportive Care	Osteoarthritis (OA)	1
4	Completed	Supportive Care	Spinal Disorders	1

Pharmacoeconomics

Manufacturers

• Purdue pharma lp
• Reckitt benckiser pharmaceuticals inc
• Bedford laboratories div ben venue laboratories inc
• Hospira inc
• Pharmaforce inc
• Barr laboratories inc
• Roxane laboratories inc

Packagers

• A-S Medication Solutions LLC
• Bedford Labs
• Ben Venue Laboratories Inc.
• Bryant Ranch Prepack
• Hospira Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Pharmaforce Inc.
• Prepak Systems Inc.
• Purdue Pharma LP
• Rebel Distributors Corp.
• Reckitt Benckiser Inc.
• Remedy Repack
• Roxane Labs
• Teva Pharmaceutical Industries Ltd.

Dosage Forms

Form	Route	Strength
Plaster	Transdermal	35 Mikrogramm/h
Plaster	Transdermal	52.5 Mikrogramm/h
Plaster	Transdermal	70 Mikrogramm/h
Film	Buccal	150 ug/1
Film	Buccal	300 ug/1
Film	Buccal	450 ug/1
Film	Buccal	600 ug/1
Film	Buccal	75 ug/1
Film	Buccal	750 ug/1
Film	Buccal	900 ug/1
Film, soluble	Buccal	150 mcg
Film, soluble	Buccal	150 ug/1
Film, soluble	Buccal	300 ug/1
Film, soluble	Buccal	300 mcg
Film, soluble	Buccal	450 ug/1
Film, soluble	Buccal	450 mcg
Film, soluble	Buccal	600 mcg
Film, soluble	Buccal	600 ug/1
Film, soluble	Buccal	75 mcg
Film, soluble	Buccal	75 ug/1
Film, soluble	Buccal	750 mcg
Film, soluble	Buccal	750 ug/1
Film, soluble	Buccal	900 mcg
Film, soluble	Buccal	900 ug/1
Solution	Parenteral
Injection	Subcutaneous	128 mg/0.36mL
Injection	Subcutaneous	16 mg/0.32mL
Injection	Subcutaneous	24 mg/0.48mL
Injection	Subcutaneous	32 mg/0.64mL
Injection	Subcutaneous	64 mg/0.18mL
Injection	Subcutaneous	8 mg/0.16mL
Injection	Subcutaneous	96 mg/0.27mL
Tablet	Oral	0.216 mg
Film	Buccal
Plaster	Transdermal
Tablet, orally disintegrating	Sublingual	1 mg
Tablet, orally disintegrating	Sublingual	12 mg
Tablet, orally disintegrating	Sublingual	16 mg
Tablet, orally disintegrating	Sublingual	2 MG
Tablet, orally disintegrating	Sublingual	4 MG
Tablet, orally disintegrating	Sublingual	8 MG
Plaster	Cutaneous	52.5 UG
Plaster	Cutaneous	5 UG
Plaster	Cutaneous	10 UG
Plaster	Cutaneous	15 UG
Plaster	Cutaneous	20 UG
Plaster	Cutaneous	35 UG
Plaster	Cutaneous	70 UG
Tablet, orally disintegrating	Sublingual	0.4 MG
Tablet
Plaster	Cutaneous	30 UG
Plaster	Cutaneous	40 UG
Plaster	Cutaneous	35 mcg/1
Plaster	Cutaneous	70 mcg/1
Plaster	Transdermal	10 Mikrogramm/h
Plaster	Transdermal	20 Mikrogramm/h
Plaster	Transdermal	5 Mikrogramm/h
Tablet, orally disintegrating	Sublingual	0.2 MG
Patch	Transdermal	10 ug/1h
Patch	Transdermal	15 ug/1h
Patch	Transdermal	20 ug/1h
Patch	Transdermal	5 ug/1h
Patch	Transdermal	7.5 ug/1h
Patch, extended release	Transdermal	15 ug/1h
Film	Buccal; Sublingual
Film, soluble	Buccal; Sublingual
Injection	Intramuscular; Intravenous	0.3 mg/1mL
Injection	Intramuscular; Intravenous	0.324 mg/1mL
Injection, solution	Intramuscular; Intravenous	0.3 mg/1mL
Injection, solution	Intramuscular; Intravenous	0.324 mg/1mL
Powder	Not applicable	1 kg/1kg
Tablet	Oral	2 mg/1
Tablet	Oral	8 mg/1
Tablet	Sublingual	2 mg/1
Tablet	Sublingual	8 mg/1
Patch	Transdermal	35 Mikrogramm/h
Patch	Transdermal	52.5 Mikrogramm/h
Patch	Transdermal	70 Mikrogramm/h
Patch	Transdermal	25 MICROGRAMMI/H
Patch	Transdermal	30 MICROGRAMMI/H
Patch	Transdermal	40 MICROGRAMMI/H
Patch	Transdermal	10 mcg
Patch	Transdermal	15 mcg
Patch	Transdermal	20 mcg
Patch	Transdermal	5 mcg
Patch, extended release	Transdermal	10 ug/1h
Patch, extended release	Transdermal	2.5 ug/1h
Patch, extended release	Transdermal	20 ug/1h
Patch, extended release	Transdermal	5 ug/1h
Patch, extended release	Transdermal	7.5 ug/1h
Patch	Transdermal	10 mcg / hour
Plaster	Cutaneous	10 MIKROGRAMM
Patch	Transdermal	15 mcg / hour
Patch	Transdermal	20 mcg / hour
Plaster	Cutaneous	20 MIKROGRAMM
Patch	Transdermal	5 mcg / hour
Plaster	Cutaneous	5 MIKROGRAMM
Injection, suspension, extended release	Subcutaneous	128 MG
Injection, suspension, extended release	Subcutaneous	16 MG
Injection, suspension, extended release	Subcutaneous	160 MG
Injection, suspension, extended release	Subcutaneous	24 MG
Injection, suspension, extended release	Subcutaneous	32 MG
Injection, suspension, extended release	Subcutaneous	64 MG
Injection, suspension, extended release	Subcutaneous	8 MG
Injection, suspension, extended release	Subcutaneous	96 MG
Patch	Transdermal	40.000 mg
Patch	Transdermal	35 mcg
Patch	Transdermal	52.5 mcg
Patch	Transdermal	70 mcg
Tablet	Oral
Tablet	Sublingual	0.2 mg
Plaster	Transdermal	10 Mikrogramm/Stunde
Plaster	Cutaneous	10 mg
Plaster	Transdermal	20 Mikrogramm/Stunde
Plaster	Cutaneous	30 MIKROGRAMM
Plaster	Cutaneous	40 MIKROGRAMM
Plaster	Transdermal	5 Mikrogramm/Stunde
Plaster	Cutaneous	5 mg
Solution	Transdermal	20 mg/patch
Solution	Transdermal	5 mg
Solution	Transdermal	10 mg
Patch	Transdermal	10 MICROGRAMMI/ORA
Patch	Transdermal	15 MICROGRAMMI/ORA
Patch	Transdermal	20 MICROGRAMMI/ORA
Patch	Transdermal	25 MICROGRAMMI/ORA
Patch	Transdermal	30 MICROGRAMMI/ORA
Patch	Transdermal	40 MICROGRAMMI/ORA
Patch	Transdermal	5 MICROGRAMMI/ORA
Solution	Parenteral	0.323 mg
Tablet		2 MG
Tablet		8 MG
Implant	Subcutaneous	80 mg/1
Implant	Subcutaneous	80 mg
Patch	Transdermal	10 MICROGRAMMI/H
Patch	Transdermal	20 MICROGRAMMI/H
Patch	Transdermal	5 MICROGRAMMI/H
Implant	Subcutaneous	74.2 MG
Patch	Transdermal	10.000 mg
Patch, extended release	Transdermal	10.0 mg
Patch, extended release	Transdermal	20.0 mg
Patch, extended release	Transdermal	5.0 mg
Solution	Subcutaneous	100 mg/1
Solution	Subcutaneous	300 mg/1
Solution, gel forming, extended release	Subcutaneous	100 mg / 0.5 mL
Solution, gel forming, extended release	Subcutaneous	300 mg / 1.5 mL
Film, soluble	Sublingual
Tablet	Oral
Tablet	Oral; Sublingual
Tablet	Sublingual
Tablet, orally disintegrating	Sublingual	2.16 MG
Tablet, orally disintegrating	Sublingual	8.64 MG
Film	Sublingual
Injection, suspension, extended release	Subcutaneous	100 MG
Injection, suspension, extended release	Subcutaneous	300 MG
Tablet	Oral	0.4 mg
Tablet	Oral	2 mg
Tablet	Oral	8 mg
Solution	Parenteral	0.300 mg
Injection, solution	Parenteral	0.3 MG/ML
Tablet		0.2 MG
Tablet		4 MG
Injection, solution	Parenteral	0.3 mg
Injection	Intramuscular; Intravenous	0.3 mg/ml
Injection	Intramuscular
Tablet	Oral	0.2 mg
Tablet	Sublingual
Patch	Transdermal	20.000 mg
Patch	Transdermal	35 mcg/h
Plaster	Cutaneous	35 MIKROGRAMM
Plaster	Cutaneous	35 mcg/h
Patch	Transdermal	52.5 mcg/h
Plaster	Cutaneous	52.5 MIKROGRAMM
Plaster	Cutaneous	52.5 mcg/h
Patch	Transdermal	70 mcg/h
Plaster	Cutaneous	70 MIKROGRAMM
Plaster	Cutaneous	70 mcg/h
Plaster	Cutaneous	20 MG
Plaster	Cutaneous	40 MG
Plaster	Cutaneous	30 MG
Solution	Transdermal	20 mg
Solution	Transdermal	30 mg
Solution	Transdermal	40 mg
Patch	Transdermal
Patch	Transdermal	35 MICROGRAMMI/H
Patch	Transdermal	52.5 MICROGRAMMI/H
Patch	Transdermal	70 MICROGRAMMI/H
Tablet, orally disintegrating	Sublingual

Prices

Unit description	Cost	Unit
Buprenex 0.3 mg/ml Solution (1 Box Contains Five 1ml Box)	46.39USD	box
Subutex 8 mg Sublingual Tabs	10.2USD	tab
Subutex 8 mg tablet sl	9.4USD	tablet
Buprenorphine 8 mg tablet sl	7.74USD	tablet
Buprenex 0.3 mg/ml ampul	6.96USD	ml
Subutex 2 mg Sublingual Tabs	5.59USD	tab
Subutex 2 mg tablet sl	5.0USD	tablet
Buprenorphine 2 mg tablet sl	4.14USD	tablet
Buprenorphine 0.3 mg/ml vial	2.96USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5968547	No	1999-10-19	2017-09-29
US5240711	No	1993-08-31	2010-11-28
CA2276170	No	2007-12-04	2018-02-24
CA2030178	No	1995-08-15	2010-11-16
US6344211	No	2002-02-05	2015-12-18
USRE41489	No	2010-08-10	2017-09-29
USRE41408	No	2010-06-29	2017-09-29
USRE41571	No	2010-08-24	2017-09-29
US6264980	No	2001-07-24	2015-12-18
US7579019	No	2009-08-25	2020-01-22
US6159498	No	2000-12-12	2016-10-18
US8475832	No	2013-07-02	2030-03-26
US8603514	No	2013-12-10	2024-04-03
US8017150	No	2011-09-13	2023-02-13
US8147866	No	2012-04-03	2027-07-23
US8703177	No	2014-04-22	2032-08-20
US8470361	No	2013-06-25	2030-05-22
US8454996	No	2013-06-04	2019-09-24
US8658198	No	2014-02-25	2027-12-03
US8940330	No	2015-01-27	2032-09-18
US9259421	No	2016-02-16	2032-09-18
US9642850	No	2017-05-09	2017-09-29
US9522188	No	2016-12-20	2035-04-24
US9655843	No	2017-05-23	2027-07-23
US9439900	No	2016-09-13	2032-09-18
US7736665	No	2010-06-15	2024-04-25
US9687454	No	2017-06-27	2029-08-07
US9827241	No	2017-11-28	2031-06-06
US9498432	No	2016-11-22	2031-06-06
US9782402	No	2017-10-10	2031-06-06
US9272044	No	2016-03-01	2031-06-06
US8975270	No	2015-03-10	2031-09-05
US8921387	No	2014-12-30	2032-01-06
US9855221	No	2018-01-02	2022-02-14
US9901539	No	2018-02-27	2032-12-21
US9931305	No	2018-04-03	2022-02-14
US10198218	No	2019-02-05	2031-06-06
US10285910	No	2019-05-14	2022-10-11
US10558394	No	2020-02-11	2031-06-25
US10592168	No	2020-03-17	2031-06-06
US10646484	No	2020-05-12	2038-06-22
US10874661	No	2020-12-29	2032-09-18
US10946010	No	2021-03-16	2032-09-18
US11000520	No	2021-05-11	2035-11-06
US11020388	No	2021-06-01	2032-09-18
US11020387	No	2021-06-01	2032-09-18
US11135216	No	2021-10-05	2029-08-07
US11433066	No	2012-09-18	2032-09-18
US11110084	No	2021-09-07	2032-07-26
US10912772	No	2021-02-09	2032-07-26
US9937164	No	2018-04-10	2032-07-26
US8545832	No	2013-10-01	2025-06-06
US8236755	No	2012-08-07	2026-07-31
US8236292	No	2012-08-07	2027-01-10
US11135215	No	2021-10-05	2032-07-26
US11839611	No	2015-11-06	2035-11-06

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	4.98	AVDEEF,A ET AL. (1996)
pKa	8.31 (at 25 °C)	AVDEEF,A ET AL. (1996)

Predicted Properties

Property	Value	Source
Water Solubility	0.0168 mg/mL	ALOGPS
logP	4.53	ALOGPS
logP	3.55	Chemaxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.42	Chemaxon
pKa (Strongest Basic)	9.63	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	62.16 Å2	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	131.76 m3·mol-1	Chemaxon
Polarizability	53.03 Å3	Chemaxon
Number of Rings	7	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9055
Blood Brain Barrier	+	0.9401
Caco-2 permeable	+	0.6893
P-glycoprotein substrate	Substrate	0.9126
P-glycoprotein inhibitor I	Inhibitor	0.5192
P-glycoprotein inhibitor II	Non-inhibitor	0.6992
Renal organic cation transporter	Inhibitor	0.5797
CYP450 2C9 substrate	Non-substrate	0.8366
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Substrate	0.8142
CYP450 1A2 substrate	Non-inhibitor	0.9153
CYP450 2C9 inhibitor	Non-inhibitor	0.8692
CYP450 2D6 inhibitor	Non-inhibitor	0.6721
CYP450 2C19 inhibitor	Non-inhibitor	0.7801
CYP450 3A4 inhibitor	Non-inhibitor	0.8322
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9212
Ames test	Non AMES toxic	0.7448
Carcinogenicity	Non-carcinogens	0.9391
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.1511 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8366
hERG inhibition (predictor II)	Non-inhibitor	0.586

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-9004200000-95c5673aa686eb387e74
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-41335c098b0866a02156
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-877684bddda5fa2f0b4c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-9bd99c6a50b2b7abafcc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-d1379b1aef0cd7ee0432
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01bc-2001900000-a94610647fcf73e5717e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-c8ddacd69887f73bbf8f
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	216.9121418	predicted	DarkChem Lite v0.1.0
[M-H]-	217.7359418	predicted	DarkChem Lite v0.1.0
[M-H]-	217.20308	predicted	DeepCCS 1.0 (2019)
[M+H]+	213.6722418	predicted	DarkChem Lite v0.1.0
[M+H]+	217.3069418	predicted	DarkChem Lite v0.1.0
[M+H]+	219.0985	predicted	DeepCCS 1.0 (2019)
[M+Na]+	214.6286418	predicted	DarkChem Lite v0.1.0
[M+Na]+	217.4496418	predicted	DarkChem Lite v0.1.0
[M+Na]+	224.87642	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.8	N/A	N/A	A18178

Details

Binding Properties1. Kappa-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Opioid receptor activity

Specific Function

G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...

Gene Name

OPRK1

Uniprot ID

P41145

Uniprot Name

Kappa-type opioid receptor

Molecular Weight

42644.665 Da

References

1. Boothby LA, Doering PL: Buprenorphine for the treatment of opioid dependence. Am J Health Syst Pharm. 2007 Feb 1;64(3):266-72. [Article]
2. Robinson SE: Buprenorphine-containing treatments: place in the management of opioid addiction. CNS Drugs. 2006;20(9):697-712. [Article]

Details2. Mu-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Partial agonist

General Function

Voltage-gated calcium channel activity

Specific Function

Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...

Gene Name

OPRM1

Uniprot ID

P35372

Uniprot Name

Mu-type opioid receptor

Molecular Weight

44778.855 Da

References

1. Kishioka S, Paronis CA, Lewis JW, Woods JH: Buprenorphine and methoclocinnamox: agonist and antagonist effects on respiratory function in rhesus monkeys. Eur J Pharmacol. 2000 Mar 17;391(3):289-97. [Article]
2. Zubieta J, Greenwald MK, Lombardi U, Woods JH, Kilbourn MR, Jewett DM, Koeppe RA, Schuster CR, Johanson CE: Buprenorphine-induced changes in mu-opioid receptor availability in male heroin-dependent volunteers: a preliminary study. Neuropsychopharmacology. 2000 Sep;23(3):326-34. [Article]
3. Sanchez-Blazquez P, Gomez-Serranillos P, Garzon J: Agonists determine the pattern of G-protein activation in mu-opioid receptor-mediated supraspinal analgesia. Brain Res Bull. 2001 Jan 15;54(2):229-35. [Article]
4. Mizoguchi H, Wu HE, Narita M, Hall FS, Sora I, Uhl GR, Nagase H, Tseng LF: Antagonistic property of buprenorphine for putative epsilon-opioid receptor-mediated G-protein activation by beta-endorphin in pons/medulla of the mu-opioid receptor knockout mouse. Neuroscience. 2002;115(3):715-21. [Article]
5. Ide S, Minami M, Satoh M, Uhl GR, Sora I, Ikeda K: Buprenorphine antinociception is abolished, but naloxone-sensitive reward is retained, in mu-opioid receptor knockout mice. Neuropsychopharmacology. 2004 Sep;29(9):1656-63. [Article]
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	4.5	N/A	N/A	A18178

Details

Binding Properties3. Delta-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Antagonist

General Function

Opioid receptor activity

Specific Function

G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...

Gene Name

OPRD1

Uniprot ID

P41143

Uniprot Name

Delta-type opioid receptor

Molecular Weight

40368.235 Da

References

1. Induru RR, Davis MP: Buprenorphine for neuropathic pain--targeting hyperalgesia. Am J Hosp Palliat Care. 2009 Dec-2010 Jan;26(6):470-3. doi: 10.1177/1049909109341868. Epub 2009 Aug 7. [Article]
2. Lester PA, Traynor JR: Comparison of the in vitro efficacy of mu, delta, kappa and ORL1 receptor agonists and non-selective opioid agonists in dog brain membranes. Brain Res. 2006 Feb 16;1073-1074:290-6. Epub 2006 Jan 27. [Article]
3. Megarbane B, Marie N, Pirnay S, Borron SW, Gueye PN, Risede P, Monier C, Noble F, Baud FJ: Buprenorphine is protective against the depressive effects of norbuprenorphine on ventilation. Toxicol Appl Pharmacol. 2006 May 1;212(3):256-67. Epub 2005 Sep 16. [Article]

Details4. Nociceptin receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

General Function

Nociceptin receptor activity

Specific Function

G-protein coupled opioid receptor that functions as receptor for the endogenous neuropeptide nociceptin. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-b...

Gene Name

OPRL1

Uniprot ID

P41146

Uniprot Name

Nociceptin receptor

Molecular Weight

40692.775 Da

References

1. Bloms-Funke P, Gillen C, Schuettler AJ, Wnendt S: Agonistic effects of the opioid buprenorphine on the nociceptin/OFQ receptor. Peptides. 2000 Jul;21(7):1141-6. [Article]
2. Lutfy K, Eitan S, Bryant CD, Yang YC, Saliminejad N, Walwyn W, Kieffer BL, Takeshima H, Carroll FI, Maidment NT, Evans CJ: Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors. J Neurosci. 2003 Nov 12;23(32):10331-7. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55